A person snowboarding down a snowy slope.

Holiday Homes in The Berkshires

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for The Berkshires holiday homes

Outdoor spa tub

1. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €331
includes taxes & fees
26 Aug - 27 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

2. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €329
includes taxes & fees
8 Sept - 9 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

3. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €260
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Coffee/tea maker, fridge, microwave, oven

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is €350
includes taxes & fees
3 Sept - 4 Sept
Home in Great Barrington
Interior

5. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is €256
includes taxes & fees
24 Sept - 25 Sept
Cozy Riverside Berkshires Retreat
Smart TV

6. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.2 out of 10, Wonderful, (5 reviews)
The price is €323
includes taxes & fees
24 Sept - 25 Sept
stylish Berkshires Retreat
TV

7. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is €487
includes taxes & fees
22 Sept - 23 Sept
Treetop Hideaway in Tyringham
Interior

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is €274
includes taxes & fees
23 Sept - 24 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

9. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €426
includes taxes & fees
23 Sept - 24 Sept
Cheerful 3-bedroom cottage with woodstove
Pool

10. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (77 reviews)
The price is €466
includes taxes & fees
26 Aug - 27 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
A heated pool

11. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is €492
includes taxes & fees
31 Aug - 1 Sept
Comfortable Berkshires retreat on mtn resort, SISO
Dining

12. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is €397
includes taxes & fees
21 Sept - 22 Sept
A roomy remodeled retreat close to MassMoCA
3 bedrooms, iron/ironing board, WiFi, bed sheets

13. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is €464
includes taxes & fees
8 Sept - 9 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Outdoor dining

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is €464
includes taxes & fees
27 Aug - 28 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Dining

15. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is €538
includes taxes & fees
26 Aug - 27 Aug
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
TV, fireplace, printers

16. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is €1,126
includes taxes & fees
27 Aug - 28 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

17. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is €431
includes taxes & fees
23 Sept - 24 Sept
The Greylock Cabin
4 bedrooms, travel cot, WiFi, bed sheets

18. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is €753
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
Exterior

19. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is €798
includes taxes & fees
22 Sept - 23 Sept
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor dining

20. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is €989
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn Near Jiminy Peak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very quiet despite being larger area than we thought. Staff at check-in helpful as our card had been corrupted .. manually entered info and we were all set! Enjoyed our balcony very much. lot of fun in the pool !"
Curt 3-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about The Berkshires

The Berkshires Holiday Homes information

Number of reviews
281
Accommodation
342 Holiday Homes
Lowest Price
€256
Highest Price
€1,126

Explore a world of travel with Expedia